The 5 Most Common Mistakes in Seasonal Hiring (And How to Avoid Them)

If you’ve ever walked into a store the day after Thanksgiving, you’ve seen the embodiment of “peak-season chaos”: shoppers everywhere, short-staffed teams, and managers trying to juggle three (or more) jobs at once. 

For many brands, Q4 means high stakes with very little margin for error. You need workers, you need them fast, and you need to keep everything compliant. Easy, right? Riiight?

Well, maybe not so much… 

Having spent 20 years in HR now, I’ve seen the same mistakes repeated again and again (and again). Even though the details sometimes change, the pain points don’t. In the end, this slows down operations, increases compliance risk, and, ultimately, frustrates your workforce.  

But here’s the good news! This is all preventable if you follow the right steps. 

Here are the five pitfalls I see most often in seasonal hiring—and, of course, how your team can try to avoid them. (P.S., if you’d like to learn more about this topic in webinar format instead, go here to see a replay of our conversation.) 

1. Misclassifying workers

I’ll start off with a surprisingly common one… 

Let’s say a brand hires seasonal sales talent as 1099 contractors, rather than W-2 employees, because “it’s only for a few months.” Fast-forward, and the IRS or state agency comes knocking. Uh-oh. 

Misclassification—treating seasonal workers as independent contractors—is one of the costliest mistakes a brand can make. And it isn’t that rare: Studies estimate that 10% to 30% of U.S. employers misclassify workers, putting them at risk for hefty penalties and back wages. 

How to avoid it: Review worker status before hiring starts. States like California and New York apply strict tests to determine who qualifies as a contractor. Don’t assume “short-term” equals “independent.” If you’re unsure (even just a little bit), get expert guidance before you post that job. 

2. Onboarding bottlenecks

If onboarding drags, good candidates don’t wait. In the webinar, I shared how we often see brands take one to two weeks (or longer) to get seasonal hires onboarded. Unfortunately, by the time forms are completed and IDs are verified, some of the best talent has already moved on. 

The holiday season doesn’t give you that kind of time. When you need talent on the floor in days, any delay can cost you the coverage you need.  

How to avoid it: Build a digital, mobile-first onboarding process. Your workforce should be able to upload IDs, sign forms, and complete training with ease. With the right system, onboarding can be wrapped up in just a few days, even with background checks. 

3. Compliance gaps

Every state has its own labor rules: minimum wage, breaks, scheduling expectations, final pay, etc. So, during peak hiring especially, it’s easy for something to slip through the cracks for many organizations.  

To put this in numbers, in fiscal year 2024, the U.S. Department of Labor’s Wage and Hour Division recovered more than $273 million in back wages and damages for approximately 152,000 workers. Seasonal hiring is a prime spot for errors simply because of the sheer volume of staff brought on in a short time. 

How to avoid it: Keep up with labor law changes in every state or province where you operate. Don’t leave it to only your managers to memorize break laws. Instead, centralize compliance tracking so updates happen automatically (a lot easier than relying on someone remembering to update a binder). 

4. Payroll chaos

Nothing erodes trust faster than paycheck problems. In the webinar, I talked about how late or incorrect paychecks are one of the biggest issues brands run into with seasonal teams. 

But beyond just the frustration for talent, keep in mind the potential compliance consequences. Some states (like California) have strict pay frequency laws, so missing a cycle there can result in fines—not to mention, an unhappy workforce, potential penalties, higher turnover… you name it. 

How to avoid it: Connect scheduling, time tracking, and payroll into one system. Pay workers on time, and at the cadence required by law. Many employers also use weekly pay to stay competitive for seasonal staff. 

5. Mishandled offboarding

Sometimes when seasonal jobs end, communication gets fuzzy. Workers get ghosted, final pay gets delayed, or nobody explains what happens next. This is all pretty risky—and, frankly, sloppy—business.  

Some states require final pay on the last day worked: i.e., you miss that deadline and you’re in violation. And from a people standpoint, seasonal staff who feel ignored are unlikely to return the next year. 

How to avoid it: Treat offboarding as part of the standard employee experience. Set clear expectations, confirm assignment end dates, and ensure final pay is processed on time. 

My takeaway

Seasonal hiring will always be fast-paced—that’s just a given. It doesn’t need to be chaotic, though. By tightening up classification, onboarding, compliance, payroll, and offboarding, you can scale faster, stay compliant, and keep your team engaged. 

FAQ

Q: Do these mistakes happen only in Q4? 

Nope. They happen year-round. But in Q4, however, the volume of hiring magnifies the risks and makes mistakes harder to recover from. 

Q: How fast can seasonal workers be onboarded with the right system? 

At AllWork, most workers are onboarded in 3–4 days, even with background checks included. 

Q: What’s the biggest mistake for brands to fix first? 

It all starts with classification. If workers are misclassified at the start, payroll, compliance, and onboarding all sit on shaky ground from there on out. 

Ready to get started?

At AllWork, we help more than 70 brands manage over 10,000 flexible workers across the U.S. and Canada. We’ve seen what works, and we’ve seen what doesn’t. With the right systems in place, even December can run smoothly. (Imagine that!) 

Schedule a demo with AllWork to see how we can help your team get ready for Q4 (and beyond).